yeah i mean from a chicago perspective specifically (which prob extends thru much of the midwest as well) this was the look of the rich white kids at my h.s. in the late 90s & at lots of suburban schools as well, but only recently became a street thing -- i think there's an aspirational wealth thing to it, or maybe its coming out of that moment where hipster & urban fashion were basically completely linked

but at least in chi the street rap (as opposed to hip-hop heads or w/e) look of high school kids is timberlands, true religion jeans, and a variety of tops: north face fleeces, american apparel hoodies, aeropostale & abercrombie shirts